The relationships between Nezirut and wine are broadly treated in Gemara and Rishonim.
We will start with Samson, Samuel and touching problem of wine in sacrifices, and later wine of Kiddush and Havdala, for the end we will discuss about wine.
Samson was a special Nazir:
The mishna in Nazir (1, 2) defines what is nezirut Shimshon, he can never cut hairs, but is allowed to being in touch with death uncleanness (see Bartenura)
For Shmuel, Machloket in Mishna:
You wrote:
Samuel was a Nazarite, but it isn't clear to me that that was so, because he doesn't make the vow, his mother makes the vow for him.
See Mishna Nazir (9, 5). According to Rabbi Nehoray, Shmuel was "Forever's Nazir" and according to Rabbi Yosse, they discuss on a verse (Shmuel 1, 1, 11). In the mishna above cited, they taught that Forever's Nazir il allowed to cut hairs with a blade every 12 months and is not allowed to be unclean. If he become unclean, he is duty to Korban tum'a as a standard Nazir.
In the discussed verse it seems (Samuel 1, 1, 11), and following the opinion of Rabbi Nehorai, there is an additional question: we see that Chana vowed that her son will be Nazir. It is apparently contradictory with the Mishna which taught in 4, 6 that a mother can not vow nezirut for her son. The Radak ask's this on the verse, Rabi Akiva Eiger on Gemara point this Radak. I have no answer.
You wrote:
But then Hannah takes some wine for a sacrifice (Samuel 1:24) after Samuel is weaned.
In the verse 24, we see that Chana was driving to Bet Hamikdash with Shmuel and with Korbanot. Korbanot contained wine "ונבל יין", Rashi itself wrote it "ונבל יין: לנסך". See more details about her Korbanot in Ralbag (Shalme Simcha, Menachot, Nesachim).
BTW Korbanot shlamim of the nazir itself need wine for libation.
Wine of Mitsva:
You wrote:
However, today we say a blessing over the wine on Friday evening, again at the synagogue at the end of the service, and Saturday morning after the service. Furthermore, at the passover seder, we drink 4 cups of wine.
See Gemara Nazir 3b-4a:
What does R`Simeon make of the statement, 'He shall abstain from wine and strong drink'? - He requires it to prohibit wine the drinking of which is a ritual obligation as well as wine the drinking of which is optional. What is this [wine the drinking of which is obligatory]? The wine of Kiddush and Habdalah, [is it not]? For them he is bound by the oath taken on Mount Sinai? - We must therefore suppose the following dictum of Raba to be indicated, [Viz.:] - [If a man says,] 'I swear to drink [wine]' and later says, 'I wish to a nazirite,' the nazirite vow operates despite the oath.
In this Gemara, (and with this choice of lecture), we see that there is no eventuality to exempt nazir from Kiddush and Havdala. Rishonim discuss this Gemara. Rabenu Tam reads the Gemara as follow: "Wine of Kiddush and Havdala? What is the problem, It is surely not bound for them by the oath taken on Mount Sinai {there are rabbinic commandments}". So Nazir does not drink Kiddush and 4 glasses of Pesach. Rambam (nezirut 7, 11) agrees with Rabenu Tam.
But the commentator in place of Rashi, (some Acharonim identified him as Rivan) learns the Gemara literally and rules that Nazir drinks Kiddush.This opinion is reported in Tosfoth Rabbi Yehuda Hachassid (Brachoth 20B) in the name of Rabbi Yosef Kara who reports himself rabbi Klonimus from Roma.
for Havdalah and last 3 glasses of Pessach nobody really thinks that they are Deorayta (scriptural).
Torah and wine
You wrote:
When in Jewish history did the grape go from something that was not holy to something that was highly venerated? What was the process, what was the
discussion, that caused the transition?
First, abstience from wine "per se" is a wrong behavior. See Nazir 19a:
For it has been taught: R`Eleazar ha-Kappar, Berabbi, said: Why does the Scripture say, And make atonement for him, for that he sinned by reason of the soul. Against what 'soul' did he then sin? It can only be because he denied himself wine. If then this man who denied himself wine only is termed a sinner, how much more so is this true of one who is ascetic in all things!
But wine is very important in human customs (around Mediterranean See).
See Berachot 35b:
Why is a difference made for wine? Shall I say that because [the raw material of] it is improved therefore the blessing is different? ... But does wine sustain? Did not Raba use to drink wine on the eve of the Passover in order that he might get an appetite and eat much unleavened bread? - A large quantity gives an appetite, a small quantity sustains. But does it in fact give any sustenance? Is it not written, And wine that maketh glad the heart of man....
Wine has a special status, see Berachot 41b-42a:
Ben Zoma was asked: Why was it laid down that things which form an integral part of the meal when taken in the course of a meal require no blessing either before or after? - He replied: Because the [blessing over] bread suffices for them. If so, [they said] let the blessing over bread suffice for wine also? - Wine is different, he replied because it is itself a motive for benediction. {Rashi explains that in several ceremonial we bless on wine, despite that our intent was not to drink wine}
But Wine is dangerous:
See the first words of The Gemara Nazir:
Seeing that the Tanna is teaching the order Nashim, why does he speak of the nazirite? - The Tanna had in mind the scriptural verse, Then it cometh to pass if she find no favour in his eyes, because he hath found some unseemly thing in her, and he reasons thus. What was the cause of the woman's infidelity? Wine. Further, he proceeds, whosoever sees an unfaithful wife in her degradation will take a nazirite's vow and abjure wine.
Nazir as a paradigm:
The relationship between sin and wine is a paradigm of behavior for a Jew as writes the Mesilat Yesharim (chapter 11):
And our Sages of blessed memory have said (Shemoth Rabbah 16:2), "The Holy One Blessed be He said, 'Do not say, "Since I may not live with a woman, I will hold he r and be free of sin, I will embrace her and be
free of sin; or I will kiss her and be free of sin. " ' The Holy One Blessed be He said, 'Just as when a Nazarite takes a vow not to drink wine, he is forbidden to eat grapes or raisins or drink grape juice, or partake of anything, for that matter, which comes from the grapevine, so is it forbidden to touch any woman but your own wife; and anyone who does touch a woman other than his wife brings death to himself.' " See how wonderful these words are! The prohibition in the case of illicit relations is likened to that in the case of a Nazarite, where, even though the essence of the prohibition involves only the drinking of wine, the Torah forbids to him anything which has some connection with wine. Through what it says concerning a Nazarite, the Torah is teaching the Sages hjw to make "a fence around the Torah" by way of implementing the authority vested in them to reinforce the Torah's rulings. Using the case of the Nazarite as a prototype, the Torah is instructing the Sages to proscribe, because of a basic prohibition, anything that is similar to it. To
reveal G-d's will in the matter, the Torah did in relation to the mitzvah of the Nazarite what it authorized the Sages to do in relation to all the other mitzvoth, namely, to forbid anything which approaches the nature of what is proscribed, by deducing what is not stated from what is stated. By applying this principle to the area of illicit relations, the Sages prohibited anything partaking of the nature of fornication or approaching it, regardless of the particular avenue of approach, whether that of deed, or sight, or speech, or hearing, or even thought.
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